High structure carbon blacks

Patent metadata

Field	Value
Publication number	US-9896583-B2
Application number	US-201615172398-A
Country	US
Kind code	B2
Filing date	Jun 3, 2016
Priority date	Jul 13, 2012
Publication date	Feb 20, 2018
Grant date	Feb 20, 2018

Abstract

Disclosed herein are high structured carbon blacks, methods of synthesis and treatment, and dispersions and inkjet ink formulations prepared therefrom. The carbon black can have the following properties: OAN≧170 mL/100 g; and STSA ranging from 160 to 220 m 2 /g. The carbon black can also have the following properties: OAN≧170 mL/100 g; and a ratio of STSA/BET surface area ranging from 0.7 to 1.

First claim

The invention claimed is:

1. A carbon black having the following properties:
OAN≧170 mL/100 g;
STSA ranging from 160 to 220 m 2 /g;
a COAN of at least 120 mL/100 g, and
a ratio of STSA/BET surface area ranging from 0.7 to 1,
wherein the carbon black is modified with at least one attached organic group.

2. The carbon black of claim 1 , wherein the at least one attached organic group comprises at least one ionic group, ionizable group, or mixtures of an ionic group and an ionizable group.

3. The carbon black of claim 1 , wherein the at least one attached organic group comprises at least one anionic group, anionizable group, or mixtures of an anionic group and an anionizable group.

4. The carbon black of claim 3 , wherein the anionic group is selected from —COO, —SO 3 − , —OSO 3 − , —HPO 3 − , —OPO 3 2− , and —PO 3 2− .

5. The carbon black of claim 3 , wherein the anionizable group is selected from —COOH, —SO 3 H, —PO 3 H 2 , —R′SH, or —R′OH, where R′ represents hydrogen or an organic group.

6. The carbon black of claim 1 , wherein the at least one attached organic group is selected from a benzene carboxylic acid group, a benzene dicarboxylic acid group, a benzene tricarboxylic acid group, a benzene sulfonic acid group, and salts thereof.

7. The carbon black of claim 1 , wherein the at least one attached organic group comprises at least one geminal bisphosphonic acid group, partial esters thereof, or salts thereof.

8. The carbon black of claim 1 , wherein the at least one attached organic group comprises at least one group having the formula —CQ(PO 3 H 2 ) 2 , partial esters thereof, or salts thereof, wherein Q is H, R, OR, SR, or NR 2 , wherein R, which can be the same or different, is H, a C 1 -C 18 alkyl group, or a C 1 -C 18 aralkyl, alkaryl, or aryl group.

9. The carbon black of claim 1 , wherein the OAN ranges from 170 to 220 mL/100 g.

10. The carbon black of claim 1 , wherein the OAN ranges from 170 to 210 mL/100 g.

11. The carbon black of claim 1 , wherein the carbon black has a BET surface area ranging from 190 to 275 m 2 /g.

12. The carbon black of claim 1 , wherein the BET surface area ranges from 200 to 270 m 2 /g.

13. The carbon black of claim 1 , wherein the BET surface area ranges from 200 to 260 m 2 /g.

14. The carbon black of claim 1 , wherein the carbon black has a COAN of at least 130 mL/100 g.

15. The carbon black of claim 1 , wherein the carbon black has a ratio of OAN/COAN ranging from 1.30 to 1.50.

16. The carbon black of claim 1 , wherein the carbon black has a ratio of STSA/BET surface area ranging from 0.7 to 0.9.

17. The carbon black of claim 1 , wherein the carbon black is a furnace black.

18. The carbon black of claim 1 , wherein the at least one attached organic group comprises the formula —[R(A)]—, wherein:
R is attached to the carbon black and is selected from arylene, heteroarylene, and alkylene, and
A is selected from carboxylic acids, sulfonic acids, phosphonic acids, hydroxyls, amines, and esters, amides, and salts thereof.

19. The carbon black of claim 18 , wherein R comprises the formula R′-Sp, wherein R′ is selected from arylene, heteroarylene, and alkylene, and Sp is a spacer selected from —CO 2 —, —O 2 C—, —CO—, —OSO 2 —, —SO 3 —, —SO 2 —, —SO 2 C 2 H 4 —O—, —SO 2 C 2 H 4 S—, —SO 2 C 2 H 4 NR″—, —O—, —S—, —NR″—, —NR″CO—, —CONR″—, —NR″CO 2 —, —O 2 CNR″—, —NR″CONR″—, —N(COR″)CO—, —CON(COR″)—, —NR″COCH(CH 2 CO 2 R″)— and cyclic imides therefrom, —NR″COCH 2 CH(CO 2 R″)— and cyclic imides therefrom, —CH(CH 2 CO 2 R″)CONR″— and cyclic imides therefrom, —CH(CO 2 R″)CH 2 CONR″ and cyclic imides therefrom, (including phthalimide and maleimides of these), sulfonamide groups (including —SO 2 NR″— and —NR″SO 2 — groups), arylene groups, alkylene groups, and R″, which can be the same or different, is selected from hydrogen, substituted and unsubstituted C 5 -C 20 aryl groups, and substituted and unsubstituted C 1 -C 6 alkyl groups.

20. The carbon black of claim 18 , wherein R comprises the formula R′-Sp, wherein R′ is selected from arylene, heteroarylene, and alkylene, and Sp is a spacer selected from —CO 2 —, —O 2 C—, —O—, —NR″—, —NR″CO—, or —CONR″—, —SO 2 NR″—, —SO 2 CH 2 CH 2 NR″—, —SO 2 CH 2 CH 2 O—, and —SO 2 CH 2 CH 2 S— wherein R″ is selected from H and C 1 -C 6 alkyl groups.

21. The carbon black of claim 18 , wherein R comprises the formula R′-Sp, wherein R′ is selected from arylene, heteroarylene, and alkylene, and Sp is a spacer derived from a compound having a reactive group selected from a carboxylic acid or ester, an acid chloride, a sulfonyl chloride, an acyl azide, an isocyanate, a ketone, an aldehyde, an anhydride, an amide, an imide, an imine, an α,β-unsaturated ketone, aldehyde, or sulfone, an alkyl halide, an epoxide, an alkyl sulfonate or sulfate such as a (2-sulfatoethyl)-sulfone group, an amine, a hydrazine, an alcohol, a thiol, a hydrazide, an oxime, a triazene, a carbanion, an aromatic compound, and salts and derivatives thereof, or any combination thereof.

22. The carbon black of claim 18 , wherein R comprises the formula R′-Sp, wherein R′ is selected from arylene, heteroarylene, and alkylene, and Sp is a spacer derived from a compound selected from 4-aminobenzyl amine (4-ABA), 3-aminobenzyl amine (3-ABA), 2-aminobenzyl amine (2-ABA), 2-aminophenyl ethylamine, 4-aminophenyl-(2-sulfatoethyl)-sulphone, (APSES), p-aminobenzoic acid (PABA), 4-aminophthalic acid (4-APA), and 5-aminobenzene-1,2,3-tricarboxylic acid.

23. The carbon black of claim 1 , wherein the at least one attached organic group comprises the formula —[R(A)]-, wherein:
R is attached to the carbon black and is selected from arylene, heteroarylene, and alkylene, and
A is selected from hydrogen, alkyls, aryls, heteroaryls, alkylene oxides, carboxylic acid esters, and glycols.

24. The carbon black of claim 23 , wherein R comprises the formula R′-Sp, wherein R′ is selected from arylene, heteroarylene, and alkylene, and Sp is a spacer selected from —CO 2 —, —O 2 C—, —CO—, —OSO 2 —, —SO 3 —, —SO 2 —, —SO 2 C 2 H 4 -O—, —SO 2 C 2 H 4 S—, —SO 2 C 2 H 4 NR″—, —O—, —S—, —NR″—, —NR″CO—, —CONR″—, —NR″CO 2 —, —O 2 CNR″—, —NR″CONR″—, —N(COR″)CO—, —CON(COR″)—, —NR″COCH(CH 2 CO 2 R″)— and cyclic imides therefrom, —NR″COCH 2 CH(CO 2 R″)— and cyclic imides therefrom, —CH(CH 2 CO 2 R″)CONR″— and cyclic imides therefrom, —CH(CO 2 R″)CH 2 CONR″ and cyclic imides therefrom, (including phthalimide and maleimides of these), sulfonamide groups (including —SO 2 NR″— and —NR″SO 2 — groups), arylene groups, alkylene groups, and R″, which can be the same or different, is selected from hydrogen, substituted and unsubstituted C 5 -C 20 aryl groups, and substituted and unsubstituted C 1 -C 6 alkyl groups.

25. The carbon black of claim 23 , wherein R comprises the formula R′-Sp, wherein R′ is selected from arylene, heteroarylene, and alkylene, and Sp is a spacer selected from —CO 2 —, —O 2 C—, —O—, —NR″—, —NR″CO—, or —CONR″—, —SO 2 NR″—, —SO 2 CH 2 CH 2 NR″—, —SO 2 CH 2 CH 2 O—, and —SO 2 CH 2 CH 2 S— wherein R″ is selected from H and C 1 -C 6 alkyl groups.

26. The carbon black of claim 23 , wherein R comprises the formula R′-Sp, wherein R′ is selected from arylene, heteroarylene, and alkylene, and Sp is a spacer derived from a compound having a reactive group selected from a carboxylic acid or ester, an acid chloride, a sulfonyl chloride, an acyl azide, an isocyanate, a ketone, an aldehyde, an anhydride

Assignees

• Cabot Corp

Inventors

• Dikan Andrew P
• Rouanet Stephane F
• Clarke Heather E
• Mackay Bruce E
• Pierre Danny

Classifications

• B01J19/26

  Nozzle-type reactors, i.e. the distribution of the initial reactants within the reactor is effected by their introduction or injection through nozzles · CPC title

• B01J2219/00177

  controlling the pH · CPC title

• C09C1/565

  comprising an oxidative treatment with oxygen, ozone or oxygenated compounds, e.g. when such treatment occurs in a region of the furnace next to the carbon black generating reaction zone · CPC title

• C09D11/324

  containing carbon black · CPC title

• C01P2006/12

  Surface area · CPC title